Synthesis of Novel Nicotinamide Adenine Dinucleotide (NAD) Analogs and Their Coenzyme Activities

被引：5

作者：

Hou, Shuhua ^{[1
,2
]}

Liu, Wujun ^{[1
]}

Zhao, Zongbao ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 32卷 / 02期

关键词：

NAD analog; pyrophosphate; bioactivity; alcohol dehydrogenase; CHEMICAL-SYNTHESIS; PHOSPHATE; ACID;

D O I：

10.6023/cjoc1106032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four methods were tested to synthesize nicotinamide adenine dinucleotide (NAD) analogs, and 5 NAD analogs were prepared. Assays of these NAD analogs indicated that malic enzyme and alcohol dehydrogenase had about 13%similar to 30% enzymatic activity in the presence of analog 3b or 3d, whereas significantly lower activities were observed in the presence of analog 3a, 3c or 3e.

引用

页码：349 / 353

页数：5

共 17 条

[1] A facile and effective synthesis of dinucleotide 5′-triphosphates [J].

Abramova, Tatiana V. ;

Vasileva, Svetlana V. ;

Serpokrylova, Inna Yu. ;

Kless, Hadar ;

Silnikov, Vladimir N. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (20) :6549-6555

[2] Chemical synthesis of the second messenger nicotinic acid adenine dinucleotide phosphate by total synthesis of nicotinamide adenine dinucleotide phosphate [J].

Dowden, J ;

Moreau, C ;

Brown, RS ;

Berridge, G ;

Galione, A ;

Potter, BVL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) :4637-4640

[3] Synthesis, conformational analysis, and biological activity of new analogues of thiazole-4-carboxamide adenine dinucleotide (TAD) as IMP dehydrogenase inhibitors [J].

Franchetti, P ;

Cappellacci, L ;

Pasqualini, M ;

Petrelli, R ;

Jayaprakasan, V ;

Jayaram, HN ;

Boyd, DB ;

Jain, MD ;

Grifantini, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (06) :2045-2053

[4] CODEHYDROGENASES .3. A SYNTHESIS OF DIPHOSPHOPYRIDINE NUCLEOTIDE (COZYMASE), AND SOME OBSERVATIONS ON THE SYNTHESIS OF TRIPHOSPHOPYRIDINE NUCLEOTIDE [J].

HUGHES, NA ;

KENNER, GW ;

TODD, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (AUG) :3733-3738

[5] A disubstituted NAD+ analogue is a nanomolar inhibitor of trypanosomal glyceraldehyde-3-phosphate dehydrogenase [J].

Kennedy, KJ ;

Bressi, JC ;

Gelb, MH .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (02) :95-98

[6]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO

[7]

2-X

[8] A chemical synthesis of nicotinamide adenine dinucleotide (NAD+) [J].

Lee, J ;

Churchil, H ;

Choi, WB ;

Lynch, JE ;

Roberts, FE ;

Volante, RP ;

Reider, PJ .

CHEMICAL COMMUNICATIONS, 1999, (08) :729-730

[9] Nicotinamide adenine dinucleotide, a metabolic regulator of transcription, longevity and disease [J].

Lin, SJ ;

Guarente, L .

CURRENT OPINION IN CELL BIOLOGY, 2003, 15 (02) :241-246

[10] A NOVEL PREPARATION OF NICOTINAMIDE MONONUCLEOTIDE [J].

LIU, RH ;

VISSCHER, J .

NUCLEOSIDES & NUCLEOTIDES, 1994, 13 (05) :1215-1216

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